Features are disclosed for generating request decision models for use by client computing devices to determine request paths or modes for content requests. The request modes may correspond to direct requests (e.g., requests made from a client device directly to a content server hosting requested content) or to indirect requests (e.g., requests made from the client device to the content server via an intermediary system). The request decision models may be trained by a machine learning algorithm using performance data (e.g., prior content load times), contextual information (e.g., state information associated with devices at times content requests are executed), and the like.